When Humphrey Met Waldorf
by Proliks
Summary: Dan wants Blair, Blair wants Dan, but that whole "friends don't kiss" thing is really putting a damper on the situation. Four different Dair scenes spanning the course of a couple of years. Title from "When Harry Met Sally". Slight spoilers. COMPLETE.
1. Chapter 1

**When Humphrey Met Waldorf**

**_disclaimer: i don't own gossip girl_**

**_an: slight s4 spoilers. depending on reaction, i have the story planned out. let me know what you all think!  
_**

**xxx**

The first time Dan almost kissed Blair, spring internships had just come to an end. There was nothing left to do but celebrate new beginnings. So, there they were on a Tuesday evening, seated in an intimate booth in Le Bernardin with a bottle of wine and scant portions of (in Dan's opinion) overly-priced hiramasa.

Taking a sip of his pinot noir, Dan couldn't help but be mesmerized by the way Blair ate, all dainty and methodical.

Like her, Dan supposed.

One curious thing about Blair's eating habits, though, was that she was apt to consume more - lots, even - when she was at ease. Oddly enough, to Dan, that seemed only to be when Blair was around _him_, of all people.

And at that moment, her plate was nearly empty.

**xxx**

As the night ticked on, Dan found the conversation to be relaxed, effortless, mutually understood. Resting his chin on his hand, a lazy grin on his face as he listened to Blair opine about transcendentalism, Dan was content.

"...so Thoreau's wife was like, 'Where's Walden?'" Blair finished, a muted excitement lacing her voice.

Dan cracked up.

"Wow, Blair Waldorf has jokes," he teased.

"Oh, absolutely," Blair smiled smugly. "They aren't as funny as that tie looks on you, though."

"Hey! What's my tie collection ever done to you?" Dan frowned, feigning hurt.

Blair cocked her head as she quipped, "Assaulted my vision, Humphrey. I believe you know that by now."

Dan didn't bother to be insulted. In fact, he was downright pleased at the fact that they shared an inside joke. Besides, he knew her humor by now, and so he countered, "Would bow-ties be better suited to your oh-so-refined tastes?"

"Very funny," Blair said dryly, rolling her eyes. "And no, they would not. Bow-ties are so last season."

"I'll toast to that," Dan said, lifting his glass.

"I'll do you one better," Blair announced jubilantly, a mischievous sparkle in her eyes. "To bright futures and the evolution of your sense of style!"

"You just couldn't resist, could you?" Dan chuckled as he drank from his glass. He rested his elbows on the table, laced his fingers together.

There was a beat of silence.

Blair's smile faded. "How could I?" she murmured, a faint (and beautiful, as Dan noted) blush racing to her cheeks. She hastily added, "While your affection towards plaid is hardly something to boast about, at least you're wearing Tom Ford instead of Target."

And right then, despite Blair's defensive quips, Dan _knew._

He leaned forward slightly, tie brushing the table. "You know, I really enjoyed working with you this semester. Seriously."

Blair met his gaze as she ran her index finger around the rim of her glass. "Surprised, are you?" she asked sarcastically.

"Well, yeah," Dan admitted, heat creeping up the back of his neck. "More than pleasantly, though. You were – _are – _great."

Eyes widened. Blair dropped her head, curls veiling her face.

Dan felt stupid.

His hand darted towards his wine glass, but before he knew it, there was another on top of his own.

Blair's.

Dan turned his head, utterly confused by the physical contact when she'd emotionally just rejected him.

"So were you," came a faint whisper.

"What? I couldn't understand you," Dan said, straining to hear Blair.

"I _said_, so were you," Blair huffed, crossing her arms. Voice lowered, Blair added hesitantly, "Great, I mean."

"Oh."

'_Oh'? Really, Humphrey?_

Stomach knotting as Blair nodded, Dan was conflicted. In the back of his mind, there was that little image of Serena, but in the front…

In the front was Blair Waldorf. His contemporary, his intellectual equal, his – well, his _crush_.

Dan's mind was made up as he observed the way Blair instinctively leaned towards him. Eyes closed, Blair's body a magnet to his own, he was going to do it.

He was going to _kiss_ Blair.

Was, being the interpretive word, because their waiter seemed to possess the curious knack of interrupting at inopportune moments.

Blair pulled back as Dan cleared his throat and shot the interloper an accidental glare. Slicked back hair and a pompous grin told Dan the guy was clearly self-important, meaning he didn't give a damn who he was interrupting - or _what_.

"I'll be back for this in a few minutes, _monsieur_," the waiter said smarmily, his thin mustache curling up with the curve of his greasy smile.

Dan nodded, smiling tightly. "Right," he replied, voice calm.

In reality, his blood was boiling. He'd taken a gamble – a word that definitely wasn't present in the Humphrey Dictionary of Moral Integrity – only to have the attempt thwarted by a modern-day Gaston.

"It – it probably wasn't a good idea, anyways."

Dan's eyebrows shot up, surprise written all over his face at Blair's sudden comment. "What? Why?"

Blair gave him an incredulous look and counted off her fingers, "There's Serena, and there's Gossip Girl, and there's –"

Holding up a hand - not bearing to hear anymore reasons why Blair found him so unworthy – Dan interrupted, "I get it, okay? You're right. We were completely, out-of-our-minds stupid, and it won't happen again. I'm sorry."

The expression on Blair's face registered hurt at his (fake) agreement, but she clutched the handles of her purse with a forced smile. "Good. Because we are _friends_, and friends don't kiss. And don't worry about the check, Humphrey. With Lily and Rufus fighting all the time, who knows for how long you'll have access to her fortune."

_Ouch. _

That one hurt.

As Blair slipped a wad of cash in the black bill holder and stalked towards the exit, Dan literally felt sick to his stomach. Why was Blair so mad that he told her what she wanted to hear?

Opening his wallet, Dan gazed at the hard-earned money inside of it. He wondered if he'd ever tell Blair how long he'd saved this semester to take her to somewhere this nice.

**xxx**


	2. Chapter 2

**When Humphrey Met Waldorf**

**_disclaimer: i don't own gossip girl_**

**_an: i'm thrilled with the response for this story and i really hope this chapter exceeds everyone's expectations! thanks, folks, for your lovely and encouraging reviews!  
_**

**xxx**

It was the first day of August, which meant that it had been nearly three months since that fateful dinner with Blair. Dan hadn't really been in contact with the brunette, save for the day he went to return Blair's money (the expression on her face when Dan told Blair he'd paid the bill himself was priceless).

Other than that, though, their connection line was all but severed - of Blair's volition, not his own.

Now, Dan was sitting on his couch on a rainy Sunday afternoon, a Hot Pocket in one hand and the clicker in his other (he lived dangerously).

Flipping through the channels before finally settling on SportsCenter, Dan briefly wondered what Blair was doing.

Being that he was the only person that knew Blair was a closet nerd (only _she_ was able correct Alex Trebek's French pronunciations and still look sexy), Dan wouldn't be surprised if she was spending her Sunday perusing the shelves at the Columbia Library.

_Or Barneys_.

Dan chuckled to himself before noticing that his phone was vibrating.

_Nate_.

He answered the call, welcoming the mindless distraction. "What's up, man?"

"Oh, you know, breaking my ankle in the middle of Central Park. The usual."

Dan raised a brow. "You broke your ankle? Congrats, dude. That takes work."

"Ha-ha," Nate said dryly. "Look, I'm at St. Luke's. Could you do me a huge favor?"

"Uh, yeah, sure. What is it?"

Noises were muffled on the other end of the line as Nate was presumably talking to the nurse. "Sorry. Anyways, Blair left her purse at the Empire the other night and I told her I'd drop it off today. Obviously that isn't happening, so could you do it for me? I'd owe you one."

Dan's mouth went dry. "O-kay," he replied hesitantly before adding, "Are Blair and Chuck back together or something?"

Nate laughed. "_Someone's_ jealous, I see. No, she isn't back with Chuck. _We _were actually hanging out. I swear, some people forget we've known each other since we were kids."

Dan breathed a sigh of relief. "Oh, right."

With the thought of Blair and Chuck together out of the way, the only notion looming in Dan's mind was how Blair was going to react upon seeing _him_ instead of Nate.

**xxx**

"I'm not hungry, Dorota!" Blair's shrill voice pierced through the door as Dan knocked.

"Uh, it's me," Dan responded, shifting in his stance awkwardly.

Silence flooded the penthouse.

The door was pulled open, and two dark chocolate eyes peeked through the crack. "Humphrey. What are you doing here?"

Holding up Blair's black Givenchy clutch like a peace offering, Dan replied, "I come bearing gifts."

Blair's eyes narrowed as she opened the door fully. Snatching the clutch from Dan's hand and crossing her arms, she did _not_ look pleased to see him. "Anything else?" she asked tersely.

Dan shrugged, not wanting to further irritate her. "I guess not."

He started to retreat towards the stairs.

"That's it?"

Dan turned around, confused. "Huh?"

Blair rolled her eyes. "You'd come all this way to deliver my clutch for Nate and there's no ulterior motive?" she huffed.

A puzzled expression crossed Dan's face. "What? Why would there be? It's not like you'd welcome me with open arms anyways."

Resting against the frame of her bedroom door, Blair looked less than amused. "You act like I hate you or something."

"No, _you_ act like you hate me," Dan replied. "Ever since dinner that night, you have, actually. But whatever, I-"

A sneeze from below caught the pair's attention.

Both Dan and Blair craned their heads to look over the banister, where a flustered Dorota was spotted trying to busy herself with a feather duster.

"Beat it, Mata Hari!" Blair screeched.

Dan silently added _Waldorf employee_ to his list of least-desired jobs. "Uh, maybe we should have this discussion somewhere else?" he suggested.

Blair looked at him suspiciously before giving Dan a slow nod. "Come in." She gestured to her bedroom.

In any other situation, Dan would be thrilled to be getting an invite to Blair's room. In this case, however, he had a foreboding sense of impending doom.

Doom, like if Blair were to tell him she never wanted to see him again.

Dan swallowed hard. He'd been right about stranger things.

**xxx**

"I don't hate you, Humphrey. I never hated you," Blair told him as she led him into her bedroom.

"Ahem."

Blair smiled. "Okay, maybe a little. But that was before I got to know you."

Dan sat down on the cushioned bench beside Blair. "Then why have you been ignoring me?" he asked bluntly.

The sound of rustling was audible as Blair pretended to look through her issue of _Vogue_. "I haven't. I've just been… busy."

Right.

Contrary to popular belief (or at least Chuck Bass'), Dan wasn't stupid.

He wasn't stupid, and he wasn't one to play games.

So, with every muscle in his body fighting against him, Dan cut to the chase. "Please don't lie to me, Blair. I'm not one of your minions." Blair opened her mouth to protest, but Dan held up a hand. "Look, I get that maybe I put you off a bit when I, you know, made a move on you. Even so, that wasn't a reason to basically throw out our friendship. We could have talked about it."

Tossing the magazine aside with an exasperated sigh, Blair closed her eyes. "There was nothing to talk about."

"Why not?"

"Because I said so."

"Gee, Blair, what an informative explanation. You should write for the _Post_," Dan joked.

Blair smacked him on the arm with a glare. "And _you_ should write for Carrot Top. He needs all the crappy jokes he can get."

"Ouch," Dan feigned injury as he rubbed his arm.

"You deserved it."

"Well, I sure as hell didn't deserve getting ditched all summer because you have the backbone of the Cowardly Lion," Dan countered.

Blair jumped to her feet, hands jammed on narrow hips. "Are you saying I'm a _coward_, Humphrey?"

Dan stood up, body mirroring Blair's as his lips formed an innocent smirk. "I'm not saying you're _not_ a coward."

"That's rich, coming from the guy who was intimidated by a sixty-year-old waiter!"

"So you're saying I _should_ have gone in for the kiss, anyways?" Dan asked, knitting his brows.

Blair pushed him lightly. "Quit twisting my words!"

"Methinks the lady doth protest too much."

Blair's mouth dropped open in shock at Dan's candor. "Don't you dare bring Hamlet into this, Daniel Humphrey!"

"Then tell me what to do!" he insisted, arms open at his sides. "Because to be honest, I'm really confused, Blair."

Dropping her gaze, Blair remained at a loss, prompting Dan to run a frustrated hand through his sheared locks. He felt it in his bones that she wanted him as much as he wanted her, yet she was doing everything in her power to fight it. He'd just - he'd have to make her see.

Drawing in a deep breath, Dan stepped forward and reached out tentatively. "Should I do this?" he whispered, tucking a silky strand of hair behind Blair's ear.

"Humphrey…" she protested weakly.

Stepping closer, Dan cupped her cheeks with two gentle hands. "What about this?"

Blair's head tilted upwards as she met his stare. Dan could feel her practically melting beneath his touch.

"Humphrey…" she murmured again, eyes fluttering closed.

His forehead pressed to hers, Dan quietly urged, "Tell me."

Blair spoke a third time. "Humphrey, I – I can't."

Confusion washed over Dan as he furrowed his brows. "Why?" he asked, his voice gentle. "I thought – have I been reading you wrong this whole time?"

Blair shook her head slowly.

"It's not that," she mumbled. When her eyes flew open, they were glassy and wet. "I'm leaving."

Dan pulled away, blindsided. "_Leaving_? What the hell are you talking about?"

Blair's bottom lip quivered as she dropped her gaze and pointed to a manila envelope that rested on her nightstand.

"It's for the best," she warned Dan as he snatched the envelope with trembling hands.

Slowly, carefully, Dan pulled a crisp piece of paper from the envelope. A blaring red emblem blazed on white paper, the letterhead of The American University of Paris. Dan knew exactly what this was.

An acceptance letter.

Yet still - and maybe this was the masochist in him - Dan wanted to hear it from her. "What is this, Blair?"

Blair busied herself with the hem of her skirt.

"Blair?" Dan pressed. He was _not _about to let her avoid the situation, not this time.

The soft mattress dipped as Blair sat on her bed. Hands folded primly in her lap, her expression controlled, she looked devoid of emotion. "I'm studying abroad. My father knows someone on the admissions board and was able to secure me a position at the University for the upcoming school year."

Dan laughed in disbelief. "You've got to be kidding me," he snorted bitterly. "You're running away?"

She was in _his _eyes, at least. Running away from Serena, from her mother.

From _him_.

Frowning, Blair crossed her arms. "I'm not running away, Humphrey."

"Then what do you call it!" Dan exclaimed, flailing his arms.

Blair jumped.

He didn't mean to raise his voice, but her obvious ploy at the avoiding the consequences of any sort of relationship with him was infuriating. Was she _that_ ashamed of him?

Blair took a deep breath, tried to keep her composure. "What I _call_ it is saving our asses."

"Right," Dan scoffed. "And how long have you known?"

"A couple of months," Blair admitted. "Look, Humphrey. It wasn't a walk in the park pushing you away all summer, and frankly, I don't want to do it anymore. It's too hard." A smile ghosted across her face before she continued, "If I leave, we don't have to worry about toeing that line. We can stay platonic, just the way we're supposed to be. I really don't want to risk losing my friends, and I doubt you do either."

"Who the hell says that's all we're supposed to be?" Dan questioned furiously.

"Common sense," Blair said bluntly. She paused before adding, "Well, Serena said something, and Chuck might have mentioned his opinion a while back, but I won't go there."

Dan felt his blood pressure rise. "_Serena_ is in no position to talk. If my memory serves me right, she fled the city because she'd already cheated with Nate. And Chuck?" Dan snorted. "I couldn't care less what he thinks. He's screwed you over so many times that it's a miracle you even take his opinion into account."

There were other choice words Dan could have used in his description of Bass ("arrogant" and "bastard" came to mind), but he left them out for argument's sake.

Dan could see Blair's eyes well up as her bottom lip jutted out. He felt a knot of guilt form in his stomach, and was compelled to apologize.

Blair beat him to the punch. "Don't say you're sorry. You aren't." She stood up, crossed the room. Leaning against the window, her figure framed in sunlight, Blair confessed something Dan never thought she'd say.

"But you're right." She rested her head against the window in a tragic move of defeat. "I don't want to be like them," Blair continued. "I _can't _be like them. The pain I felt when Serena admitted she slept with Nate was like being stabbed in the chest. I won't make anyone go through that. Even if…"

Dan stepped towards Blair, his heart aching at her admission. "Even if what?" he asked softly.

"Even if being with you would make me happy," Blair finished.

Mouth dry, Dan couldn't find the right words to comfort her.

Instead, he walked slowly to the window.

Standing before Blair, in all her heartbreaking beauty, the only thing Dan could do was wrap his arms around her and hold her close.

He felt Blair's head press against his chest, heard the soft sigh emitted from her lips. Resting his chin atop dark tresses, Dan knew that this moment defined the way he wanted to live the rest of his life.

But the moment was shattered with Blair's next words.

"I guess this is goodbye."

**xxx**


	3. Chapter 3

**When Humphrey Met Waldorf**

**_disclaimer: i don't own gossip girl_**

**_an: my university gave us a snow day, so i spent all day perfecting this chapter. it's super long, but all the more to read, right? i love that you guys love this story. your reviews encourage and inspire me, so thank you!_**

**xxx_  
_**

It was April 1, also known as April Fool's Day.

_Also_, and more _importantly_, it was known as the day Blair Waldorf was set to come home for spring vacation.

Dan had been counting down the days

N_ot _that it mattered or anything. He preferred to think that in between being a savior to Serena and a workout buddy to Nate, there was no time left to be a fool for Blair. Five or six… okay, seven…teen emails back and forth to each other meant little in the grand scheme of things, at least to Dan.

Still, the time had come where Blair would soon be stepping on American soil, and Dan found himself terrified.

**xxx**

_**Spotted: The long-lost Blair Waldorf, holding more than shopping bags on her arm. Have you finally found your Prince Charming, B? **_

**xxx**

The blast came swiftly, unexpectedly, yet news spread across the Upper East Side like a wildfire.

When he read it, Dan nearly fell off of his chair smack in the middle of a crowded Starbucks. The raspberry scone sat like a brick in his stomach as he realized the implications of what was happening.

Blair had a boyfriend.

A _French_ boyfriend, who probably sang her love songs in his native tongue.

_Tongue_.

Blair was being kissed by someone who _wasn't_ Dan.

Of course she wouldn't have told him. She knew he'd be crushed, especially hearing it from her. But still, as he swirled his coffee around in his mug, Dan couldn't help but feel betrayed.

Life just wasn't fair.

**xxx**

On the heels of Blair's arrival came Nate's acceptance letter to Harvard's School of Law. Of course, as was custom on the Upper East Side, there was a party in his honor.

Dan couldn't believe that his best friend actually got accepted. He suspected Nate's luck depended highly on the state of connections between Grandfather and the Board of Admissions. Still, Nate was his buddy, and Dan knew it would be remiss of him to skip the soiree.

Which is why Dan was in the process of picking out a shirt to go with his blue and black tie (he always decided on the tie first. The Humphrey men were peculiar in that way).

Settling on a simple light blue shirt, Dan found himself dressed rather quickly. With his hair cut close to his scalp, there was little else to be done before venturing out to Anne Archibald's for the party.

But Dan, he knew Blair would be there, just knew it. Perhaps that's why he was a bit more selective in his cologne choice (never before did Dan think his most pressing issue would be deciding between Terre D'Hermes and Armani Code).

The last time he wore the Armani, Blair had left him for France.

Dan remembered, because he hadn't worn it since. Not that he was the most superstitious person in the world, but that cologne? It was bad luck.

So Terre D'Hermes it was.

With a couple sprays on the neck and wrists, Dan was out the door.

**xxx**

The Archibald home was ornate and expansive. It was everything an upper-class dwelling should be, and more.

Dan found himself overwhelmed as he stepped through the front door. He'd never been to Anne's before, namely because Nate had moved out before Dan had become friends with him.

The wooden floors were perfectly polished, the portraits on the wall straight as a pin. If Dan were to venture a guess, he'd say that Anne Archibald was one meticulous lady. He'd also wonder where along the line that trait got lost, because Nate's preferential mode of living involved shirts hanging off of lampshades.

Awkwardly wandering through the halls, Dan soon found the main room. Wall to wall, it was brimming with Manhattan royalty.

And speaking of royalty, there, across the room beside a laughing Blair, was Prince Charming.

Dan instinctively rolled his eyes.

Luckily for him, a member of the wait-staff stepped in front of his view of the happy couple. "Champagne?" he asked with mock cheer.

"Oh, yeah. Thanks," Dan replied gratefully, grabbing a flute of the bubbly liquid.

He saw another hand dart out and grab a flute as well. Turning, Dan was surprised to see a stony-faced Chuck.

_Great_.

"Dan." Chuck paused to down his champagne, his Adam's apple bobbing as he swallowed. Setting the glass on the table behind them, he continued, "I'm surprised to see you here, considering the fact that Lily and Rufus' divorce warrants you free from the shackles of high society."

Dan shrugged, sipped his beverage. "I'd be a pretty lousy friend to Nate if I didn't come."

"Well aren't you sweet?" Chuck drawled with a smirk.

Pressing his lips together in a thin line, Dan didn't answer. His distaste towards Chuck (and vice versa) was particularly well-known amongst the Upper East Side's various social circles, and really, Dan just wasn't in the mood for this – this _chat_ thing, if one could even call it that.

Instead, he drew his attention to Blair and Prince Charming. He was tall, sandy-haired, and obviously possessed a sense of humor; Blair's giggles could be heard from across the room.

Out of his peripheral, Dan saw Chuck watching, too.

No surprise there.

What _was_ surprising was that Chuck actually spoke again. "It's an enviable position to be next to her," he commented, so soft that Dan barely heard it.

But he did, and Dan really wasn't sure what to say. He'd never had a real conversation with Chuck before. "I – yeah. Yeah, I guess it is."

"You _guess_? Please," Chuck snorted. "You've been dying to get your hands on Blair ever since the W internship. I would have thought you'd realize by now that she doesn't want you."

Rubbing the back of his neck, Dan blushed. He really didn't want to get into this with Chuck, but… "Obviously she doesn't want _you_ either, so I'm not sure what you're trying to get at."

Chuck was silent for a long moment, and Dan suddenly felt uncomfortable. Like, walk-in-on-Rufus-and-Lily-having-_sex_ uncomfortable.

"Blair and I have come to an understanding," Chuck said suddenly. "And while we've both agreed that we're better as friends, I still care about her and her best interests. You see, dating princes might _seem_ glamorous, but I don't think Blair will benefit much from it in the long-run."

Dan's mouth fell open at the revelation. "Wait, he's actually a _prince_? You can't be serious."

"I wish I weren't." Chuck reached for a caviar-topped cracker as a server passed. "But he's a Grimaldi." At Dan's confused expression, Chuck continued, "Which translates to French royalty for the uninformed. And if Blair's attachment at his hip is any indication, he'll be courting her overseas for much longer than a school year."

Nausea rose to Dan's throat.

As he observed Blair more closely, he knew that Chuck was on to something. While still as gorgeous as ever, Dan estimated that she'd lost about ten pounds.

Ten pounds that looked like twenty pounds from her already small frame.

And knowing Blair - which he most certainly did – she was doing everything in her power to be as perfect as possible for the Prince (and French press).

The notion was ridiculous even as Dan contemplated it, because Blair was already perfect, and he was sure that the Prince would agree. But Blair was also stubborn, and when she had an idea in her head, she would follow through to the end.

Dan shook his head sadly.

"You see it, too?" Chuck's raspy voice stirred Dan from his thoughts.

He nodded reluctantly. "Yeah. Yeah, I do."

"She's not –"

"Comfortable," Dan finished, eliciting an impressed look from Chuck.

"I thought I was the only one that could tell."

Dan grinned mutedly. "Not surprising. Reading Blair Waldorf is far from an easy feat."

"True." Chuck nodded in agreement as he smoothed the lapel of his black jacket. "Look, Dan. I don't particularly care for you and I'm aware that the feeling is mutual."

As they both glared at Blair fawning over the man beside her, Chuck added in a low pitch, "But we both know she isn't as happy as she lets on. And for some strange reason, she listens to you. So, if you can convince her to rethink her current relationship, you've earned my respect, dubious though it might be."

With those words, Chuck disappeared into the crowd, leaving Dan supremely dumbfounded.

The arrogant prick had a point, though.

Encouraged, Dan weaved through the throng of people towards Blair. He approached her with butterflies fluttering (no, _kamikaze-ing_) in his belly.

"Humphrey!" Blair exclaimed, Eleanor giving her a disapproving look.

Despite the presence of the Prince, Dan couldn't contain the huge grin spreading across his face. "Hey," he breathed as he gave her a long hug. Blair's hair still smelled exactly like the Alterna shampoo she'd always used; it was a welcome familiarity. "How's France treating you?"

Blair's hand lingered on his shoulder as she pulled back. "It's been amazing. But I'm glad I'm getting a break. There's only so much shopping and pastry-eating a girl can do."

Dan knew Blair wasn't doing any of the latter, but he gave her a warm smile anyways. "Awesome, Blair. Really."

"Yes, _Louis_ has made my daughter very happy." Eleanor's voice made both Dan and Blair jump.

"And that would be me," Louis smiled, slightly embarrassed at the awkward use of his name. "Pleased to meet you… Humphrey, was it?"

Louis stuck out his hand.

Hesitantly, Dan outstretched his own and gave a firm shake. "Dan, actually." Looking to Blair, he added, "You know, I was hoping to talk to Blair for a minute. To catch up and stuff."

Eleanor appeared to begin protesting when Louis answered, "Yes, of course. Blair must be dying to see old friends."

Blair gave Louis a reassuring smile. "I'll be back shortly."

**xxx**

Leading the way out of the main room, Dan really wasn't sure whether to start with her alarming weight loss or the fact that she's dating someone who would never move to her country.

He went with the former.

And, as usual, Blair went on the defensive. "I have no idea what you're talking about, Humphrey. I'm the exact same size as I was when I left. And don't even ask what that size is if you value your manhood."

"Blair, you're lying," Dan answered pointedly. "And I'm worried about you. So is Chuck."

At the last revelation, Blair's eyebrows shot up. "_You_ talked to _Chuck_?"

Dan couldn't help but chuckle. "Yeah. Hell froze over, I know. But as it turns out, we have something in common."

"What, you've both made a hobby of critiquing my weight?" Blair snapped.

"It's not about that, Blair," Dan defended himself. "It's about you dating someone you can't even be yourself around. And if you can't be yourself around him, then you don't really love him. And maybe – maybe you shouldn't be with him."

Blair crinkled her nose. "That's not true."

"So you love Louis because…."

"Because he's handsome and kind and he has impeccable fashion taste, unlike someone I know."

"I see you haven't left your sense of humor in France," Dan noted, sitting down on the leather black couch centered in Anne Archibald's great room.

Blair followed suit, situating herself on the other end of the couch and crossing her legs primly. "Of course not. You just tend to bring it out of me." With a satisfied smirk, Blair leaned back into the couch. She was quiet for beat, her face growing serious. "Look, you don't need to worry about me. I'm perfectly happy, contrary to yours and Chuck's beliefs."

Dan raised a brow, incredulous.

"I _am_," Blair insisted.

"I know you, Blair. And I know you don't eat when you're in your 'impress the masses' mode."

Blair eyed Dan innocently. "I can't help it that French food is much leaner than American."

Unable to stifle his laugh, Dan snorted, "Oh, come on, Blair! They don't make croissants with broccoli and kale!"

"_Fine_!" she huffed. "I haven't had an appetite lately. Happy?"

The smile from Dan's face disappeared. "Of course not, Blair. I just – I want you to be honest with me. And with yourself, most importantly. Why are you _really_ dating Louis?"

Blair sighed, ran a finger through soft curls. "Can't a girl date a prince without facing the Humphrey Inquisition?"

"Not a chance," Dan said with a lopsided grin.

"Well, what would you like me to say?" Blair questioned. "He's got the face of Jack Dawson with the wealth and prestige of Cal Hockley. _And_ he's nice. I just need some time to get used to dating a Grimaldi, that's all."

Dan cringed.

"I'm glad you select your dating partners based on characters from James Cameron films," he observed drolly, before adding, "Look, Blair. If you insist on dating the guy for now, fine. I can accept that. But I what I can't accept is you not taking care of yourself. And I _really_ don't want to accept you staying in Paris longer than this semester warrants."

A sad, fleeting smile crossed Blair's face. "I can't promise you that."

"Of course you can't," Dan bites out, harsher than intended. He was a wounded animal, lashing out.

A stupid, embarrassed, pathetic, wounded animal.

All because his heart had to be difficult and beat only for Blair fucking Waldorf.

The same Blair fucking Waldorf that refused him time and time again.

Well, this time? This time, Dan was done. He –

He felt a hand on his knee, heard a murmur in his ear. "Why do you do it, Humphrey?"

Mouth dry at the feeling of Blair's hot breath on his neck, Dan stuttered, "W-what?"

"Why do you still try? I'm not worth the trouble."

Dan's torso twisted as he turned to Blair to meet wide, searching eyes. "Blair," he said quietly, running a hand up her thin arm, "you're worth it. You. Are. Worth. It. You're the only one that doesn't believe it."

Blair smiled, leaned into his touch. Her fingers strolled up Dan's crisp shirt, playing with the buttons along the way. "You think so?" she whispered.

"I know so."

Blair's eyes, those big, brown, sparkling eyes, searched Dan's face, gauging his honesty. "You're something else, Humphrey," she murmured, her penetrating gaze falling to his lips.

Dan's brain, normally functioning at a rational and moralistic level, was racing with thoughts that would make a Sunday School teacher blush.

He swallowed thickly.

"Uh, th-"

Dan was cut off as Blair's lips crashed furiously against his own. It was a starved kiss, hungry and eager, and Dan's lips were more than willing to part for the soft velvet tongue that begged for entrance.

He could taste her.

Champagne and strawberries mixed with the faintest hint of mint.

Hand winding through Blair's hair, Dan pulled her closer, desperate for more.

His heart was pounding madly against ribcage, his mind a jumbled mess save for a single blaring thought.

Blair was kissing him.

_Him_, not Chuck, not Louis –

Not Louis.

"Leave him, Blair," he breathed against her ear.

Blair crawled in to Dan's lap, planted ravenous kisses up and down his jaw-line.

"Blair…" Dan protested. Knowing that Louis was just a few rooms over, Dan's moral compass was spinning hopelessly out of control. Still, with Blair's hands fumbling at his belt buckle, it was pretty damn hard to keep on his high horse.

His fingertips traveled up creamy thighs, stopping just short of the lacy hem of Blair's La Perlas. "Blair," Dan breathed, "I want this so badly."

"Me too," she gasped against the roughness of Dan's hand.

What happened next, Dan would probably regret until his dying day.

He pulled back.

Blair, hair disheveled and lipstick smudged, stared at Dan expectantly.

"I want this, Blair," he repeated, "but I want it when you're here, for good. Without Louis."

Hurt was written all over Blair's face at Dan's rejection, and he quickly rushed to console her. "Blair, I guarantee you it's killing me to do this. I've been ready to be with you for the past year, and if I have to wait a little longer to do that, then fine. Like I said before, you're worth it."

Dan's reassurance did nothing to ameliorate Blair's dissatisfaction.

She got off of Dan and stood up, smoothing the wrinkles out of her dress. Not meeting his gaze, Blair said nonchalantly, "Fine, Humphrey. Whatever you say."

Dan jumped to his feet, put a hand on her shoulder.

Blair recoiled. "Don't touch me. You have to _wait_, remember?"

Sighing, Dan ran a hand through his hair. "Blair, come on. You gotta understand where I'm coming from. I like you way too much to sneak around with you behind everyone's backs. You deserve better, and you know what? _I _deserve better."

Blair rolled her eyes begrudgingly. "I _get_ it, Humphrey. Your chastity belt comes off with our blacklisting from S and Chuck's lives."

The bluntness of her statement made Dan laugh. "Yeah, that pretty much sums it up."

As Blair walked to the door, her fingers lingering over the knob, she looked over her shoulder and gave Dan a wistful smile. "Maybe another time."

And for the third time in his life, Dan watched Blair leave without knowing if she'd ever talk to him again.

It was the nature of their relationship.

Dan pushed, Blair pulled. Blair pushed, Dan pulled.

Somehow, though, Dan knew they would eventually meet at the middle.

**xxx**

.


	4. Chapter 4

**When Humphrey Met Waldorf**

_**disclaimer: i don't own gossip girl**_

_**an: i'm really sorry about the wait, but i didn't want to publish this until i was satisfied. i hope this last chapter satisfies all of you as well! can i just say i was so happy and surprised that the show used the harry/sally comparison? a sign of things to come, i hope!**_

**xxx**

"You know, I'm not much of a designer snob, but I gotta admit Marc Jacobs makes a comfy button-down."

"Wow, Humphrey, impressive. Shopping along Fifth Avenue without Serena or me holding your hand!"

"Yeah, I'm a big boy now,"' Dan laughed, examining a pair of black-framed fashion glasses. "I wish you could see these specks, Blair. I'm telling you, fashion at its worst."

"I'm sure the dictator of taste would agree," Blair replied, smile evident through her tone.

It was exactly two years to the day that Dan had last seen Blair, now a permanent fixture in the French media due to her relationship with Louis. Dan, on the other hand, had his hands full as founder and director of the New York Writers' Society, an organization that offered creative writing workshops to aspiring authors from all walks of life.

Needless to say, Dan was doing just fine professionally. His love life, on the other hand? A complete and total mess.

After Blair left, Dan found himself in a depressive funk. So depressed, in fact, that Nate had to physically _drag_ Dan out of the loft in order to get the latter a little natural vitamin D.

So, naturally, when Serena came prancing around again, all long legs and shiny hair and dimwitted smile, Dan couldn't help but seek refuge in familiarity.

His heart just wasn't in it, though, and Dan's incredible feeling of guilt had prompted him to confess to Serena his love for Blair. The blond had taken it a lot better than Dan thought she would; only minor damage was caused to his beloved book collection.

Serena had gotten over it relatively fast, though, as Nate (with Dan's approval) was there to pick up the pieces.

The next woman that entered his life had been an auburn-haired graduate student named Samantha. She was cute, something of a bookworm, and also happened to be a stage five clinger who had the oddest way of knowing exactly where Dan was at any time of the day.

It was safe to say that after Sam the Stalker, Dan had sworn off relationships altogether (barring the occurrence of a miracle whereby Blair actually followed her heart and gave up her delusions of becoming a real-life princess).

Yep, as Gossip Girl still loved to point out, Dan Humphrey was currently sitting pretty at the head of the Single and Sullen table.

Still, his weekly phone calls from Blair made him feel like less of a Lonely Boy, because even though it was torturous for Dan to know she was taken, it was even more torturous not to talk to her.

They joked a little longer about Marc Jacobs' unfortunate glasses design before the conversation lapsed into a heavy lull. It was an ominous quiet, nothing like the easy camaraderie Dan and Blair used to share when they'd grown tired of talking.

"Dan," Blair said suddenly, breaking the silence.

The use of his first name was _not _comforting.

"Yeah, Blair?" he asked.

Blair's voice wavered nervously on the other end of the line. "I have to tell you something, and I want you to promise you won't freak out or get mad. Can you do that?"

Swallowing thickly, Dan shook his head, forgetting that Blair could not see him. Making a bee-line towards the store's exit, Dan pushed through the glass doors, the rush of fresh air welcoming.

"Dan?" she repeated.

"Uh, yeah. Whatever," stammered Dan as he leaned against a glass window display.

Blair took a deep breath and her next few words hit like a ton of bricks. "I'm engaged."

Wordlessly, Dan hung up.

**xxx**

"Oh, man, I'm really sorry," Nate sympathized, offering Dan a Sam Adams from the fridge. "So, what are you gonna do?"

Dan accepted the beer as he slumped deep into the cushion of his favorite chair. "What do you mean what am I gonna do? What _can_ I do?"

Nate flopped onto the couch with an optimistic smile. "Come on, dude, you're the classic movie buff. The chicks in those movies always go nuts for the guy that interrupts weddings and confesses his undying love!"

Swigging his beer, Dan shook his head. "Yeah, well, I'm not taking the chances of public humiliation seeing as Blair's turned me down what, three times now?"

Nate winced. "Ouch. But still, what could it hurt? I –"

The blond was cut off by the sound of Dan's phone ringing.

Dan picked up his cell, saw the name across the screen.

**Blair**

He let the phone go to voicemail and was met with a quizzical look from Nate. "Waldorf," Dan explained.

Groaning, Nate put a hand to his face. "Dan, if you don't talk to her, you guys are _never_ gonna work things out. Trust me, I've ignored enough girls to know."

"I'm pretty sure Blair getting married is what's making things not work out," Dan remarked tonelessly, reaching for the remote and turning on the television. "I'm done talking about this, but you're welcome to stay for a night of basketball and beer."

Nate shrugged, gave his friend a reassuring grin. "Sure, man. Sounds great."

**xxx**

"Dude," Nate slurred, one game and twelve beers into the night, "you are my fest briend. Best friend, I mean." He looked at his watch, squinted. "Hey, it's only… one, I think. Wanna go meet up with Serena at Socialista?"

Dan dropped his head back, drunk and tired. "That's probably the worst thing I could do right now, man. I'm gonna – I'm gonna sleep," he managed to get out.

Nate looked disappointed for a second, but then his brilliant blue eyes sparkled mischievously. "I guess S and I could use a little time to ourselves, eh?"

"Go for it it," Dan encouraged.

"I think I will." Standing up and stumbling towards the door, Nate gave Dan a wave. "Later, man."

"Later," Dan reciprocated unenthusiastically. He pushed himself out of the chair, phone in hand, and shuffled towards his bedroom.

Flopping on to the bed, fully dressed, Dan stared at his cell.

It taunted him, full of messages from Blair.

_Blair._

Who did she think she was, jetting off to Paris to live her fairytale life?

Dan supposed he couldn't blame her for living out every girl's dream. Besides, he was a pauper. He couldn't offer her prestige, power, and influence the way Louis could. And isn't that what Blair's always wanted? To be a powerful woman?

Dan sighed, body buzzing from the alcohol.

He definitely didn't plan to have things go this way with Blair, but they did, and now he's drunk, and what was it they said about alcohol?

Oh, right.

Liquid courage.

Scrolling down his contact list, Dan stopped at **Blair**, pressed "call" without thinking twice.

The line rang once. Again. Three times before a groggy voice answered the call. "Hello?"

"Blair," Dan slurred, rolling onto his back and closing his eyes to drink in her voice.

Blair suddenly snapped out of her tired state. "Humphrey, what the hell? It's six thirty in the morning here!" she whispered fiercely.

Dan struggled to understand Blair in his drunken state. "Wh- what?"

"Are you _drunk_?" Blair hissed into the receiver.

"Maaaybe."

"Where are you?"

"Loft."

Blair sighed in relief.

Dan's voice cracked, dehydrated. "I miss you, Blair. Come home."

Silence for one, two, three, seconds. "I have to go."

And the line went dead.

**xxx**

Dan woke up the next morning with a splitting headache, regret, and… a text message?

Squinting to read it, Dan realized it was from Blair. He didn't even want to read it, especially if it had anything to do with yesterday's phone call, but…

_I'm worried about you. Please call me, sober this time preferably. _

Running a hand through his hair, Dan wondered what he would even say to Blair. He was so… so _mad _that she would disregard their bond the way she had.

He gave himself time to think as he jumped in the shower and washed the memory of last night away.

**xxx**

"I'm glad you called, Humphrey." Blair sounded genuinely relieved when she answered his phone call thirty minutes later.

Dan exhaled, leaned against the kitchen island. "I can't say it was an easy decision."

"Well, it certainly seemed easy for you last night," Blair replied casually.

Dan winced. "I don't drink often."

"Clearly," she snapped, before softening her tone. "I didn't want to tell you like that, I'll have you know."

"I'm glad you did," Dan admitted, grabbing an apple from the fruit bowl and rolling it on the table. "Look, Blair, I'm not gonna rehash my feelings for you. You're a grown woman and you're making your own decisions. If you really want to marry Louis, if you really love him and want to spend the rest of your life with him, I'm not going to stop you. Just promise to leave my wedding invite out of the mail."

Blair seemed taken aback by Dan's bluntness. "You aren't coming?"

"I'm not coming," he echoed.

Dan hated being harsh, but he had to think of himself for once. And if he went to that wedding, there would be a large chance his heart would be rendered irreparable.

"Oh," Blair faltered.

"Sorry, Blair, but you have to understand where I'm coming from…"

"I understand perfectly," she replied saccharinely, feelings clearly hurt.

Dan felt uneasy in the conversation and quickly rushed to end it. "Look, I have a call on the other line, but… good luck, Blair."

He didn't mean it.

Blair sniffled, voice cracking with emotion, "Bye, Humphrey."

**xxx**

Early September meant the wedding of Louis Grimaldi and Blair Waldorf.

It was as if the entire Upper East Side had been evacuated, as all of the area's wealthy residents were en route to Paris for the ceremony. Brooklyn, however, was still occupied by a very irritable Dan.

Nate and Serena had begged him to go with them to France, but he'd refused, citing a busy afternoon (hey, the New York Times crossword puzzle is not an easy feat to complete).

And so, here Dan was, alone in his loft while the world was getting ready to celebrate Blair's wedding.

**xxx**

By the next morning, Dan was resigned to the idea that Blair Waldorf was now Blair Grimaldi. He consoled himself with a cup of hot tea and perused his favorite internet blogs before taking a long jog around the borough.

Dan returned home to hear his phone ringing.

He was inclined to go jump in the shower right away, but something told him cutting off social ties was probably not the best way to start getting over Blair.

Not bothering to check who it was, Dan answered the call with a brief, "Hello?"

Frantic, heavy breathing greeted him back, followed by a ragged, "Humphrey?"

Dan's heart stopped.

"Blair, what's going on? Are you okay?" he asked, body fueled with concern.

On the other end of the line, Blair burst into tears.

_That's a no_.

"Okay, Waldorf, you need to calm down. Breathe," Dan coached her soothingly."Why are you crying?"

Blair's sobs turned to sniffles. She hiccupped. "I'm so stupid. So, so, so _stupid_!"

"You aren't stupid, Blair," Dan scolded her softly. "Stubborn, bossy, prideful, yes. Stupid? Absolutely not." Relieved when he heard Blair laugh a little, Dan continued lightly, "So, what's up princess?"

"I'm not a princess."

"Uh, sorry, but I think my phone's breaking up or something. What did you just say?"

"I said I'm not a princess," Blair repeated, her voice steadier this time around.

Dan froze at the implications.

If she wasn't a princess, she wasn't a Grimaldi, which means… "You – you didn't get married?"

"I almost did," Blair admitted breathlessly. "I wore the dress, walked down the aisle, listened to him say 'I do', but when it was my turn, I… I couldn't do it. Because," she said, intensity dropping, "because everything that I was supposed to say to Louis, I wanted to say to you. I love you, Dan."

Dan was at a loss for words.

Here he was, dripping with sweat in the middle of his loft, with Blair pouring her heart out to him via telephone. For some reason, Dan doubted even Shakespeare would be able to come up with some romantic speech in this situation.

"Are you there?" Blair asked anxiously.

"Uh, yeah. Yeah, I'm here, sorry," Dan replied, shock wearing off. "I just can't believe this, you know? I've been waiting to hear this from you for so long. Now that you have, I'm just – I'm so mind-numbingly, overwhelmingly happy that I don't know what to do."

"You could say it back," Blair replied, daring playfulness.

Laughing, Dan's nerves disappeared. "You already know I love you Blair. I've loved you for years. The only thing I could ask for right now is to say it to you in person."

"Give me two days and I'll be there."

**xxx**

Dan rolled around restlessly in his bed.

He'd slept for a little while, but anxiety kept deep slumber far away.

A faint knocking at the door prompted Dan to jolt up in bed, a million different scenarios passing through his head.

Slowly, he got to his feet.

The knocking became more persistent, eliciting a loud "Coming!" from Dan.

When he opened the door, Dan was convinced he was dreaming, because there she was.

Blair _Waldorf_, with her glossy hair pulled back in a lazy ponytail, her eyes puffy and tired, was standing in the doorway. "Hi," she whispered, drained.

Dan stepped back and let Blair in, stunned. "Blair, I – what are you doing here? I thought you said to give you two days."

Dropping the handles of her Louis Vuitton luggage, Blair let her suitcase fall to the ground. "I couldn't wait that long."

Dan shook his head, a wistful smile on his face. Leave it to Blair Waldorf to show up unexpected at three in the morning. And leave it to Blair Waldorf to look absolutely, breathtakingly gorgeous even barefaced with messy hair.

"I couldn't either," Dan told her, drawing Blair against his chest protectively. "Are you okay? I imagine ditching a prince in front of thousands of people isn't easy on a girl."

Blair inhaled against his neck. "Mm, I'm only the Hester Prynne of Paris. It's nothing I can't handle."

Kissing the top of her head, Dan felt a surge of happiness course through his veins. "Well, it's a good thing you don't live in Paris anymore then, is it?"

"A _very _good thing," Blair agreed. She pulled back, looking up at Dan with a smile. "So, wasn't there something you were supposed to tell me?"

"Hmm," Dan pretended to think. "Oh, right. See, there's this girl I know. She's beautiful and smart and makes the best pumpkin pie I've ever had. She kinda loves me."

"Is that so?" Blair asked with a giggle. "I'm guessing you _kinda_ love her back then, huh?"

Bending down, Dan slipped one arm around Blair's back and another behind her knees, scooping her up. As he carried her to his room, slamming the door behind them with his foot, Dan replied, "You better believe it."

**xxx**


End file.
